Potassium Carbonate → HCID 66649426, compound

HRID 420165Notes

Reaction equation

HRID 420165 reaction equation
CB(O)O.[C:5]([O-])([O-])=O.[K+].[K+].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([N+:32]([O-:34])=[O:33])[C:23]=1OS(C(F)(F)F)(=O)=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C1COCC1.O.CCOC(C)=O.Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:5][C:23]1[C:22]([N+:32]([O-:34])=[O:33])=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][C:13]=1[O:12][CH3:11]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 86621576HCID 86621576, compound

Product 1

HCID 66649426HCID 66649426, compoundYield 78.6%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4.92 g of MeB(OH)2, 33.9 g of K2CO3, 25.6 g of ethyl 3-methoxy-5-nitro-4-{[(trifluoromethyl)sulfonyl]oxy}benzoate in 500 ml of THF and 50 ml of water was added 5.03 g of PdCl2 dppf and the mixture was stirred under argon atmosphere at 80° C. overnight. The mixture was diluted with AcOEt and water, filtered through Celite and the filtrate was extracted with AcOEt. The extract was washed successively with saturated NaCO3aq and saturated brine, dried over Na2SO4, and concentrated. The residue was purified on SiO2 column chromatography and the fractions containing the intended compound were concentrated. The resulting solid was washed with n-hexane and dried to give 12.9 g of the intended compound as a yellow solid.

Workup

  1. filtrationfiltered through Celite
  2. extractionthe filtrate was extracted with AcOEt
  3. washThe extract was washed successively with saturated NaCO3aq and saturated brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified on SiO2 column chromatography
  7. additionthe fractions containing the intended compound
  8. concentrationwere concentrated
  9. washThe resulting solid was washed with n-hexane
  10. customdried

Sources & evidence

ORD record
ord-0dcb5a63f1ff4acbafc2e2fc18b217c4
Source dataset
uspto-grants-2012_01
Patent number
US08093389B2

Reaction notes

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